HCID 13772986, compound → HCID 13772988, compound

Participants

Reaction Steps

A suspension of 100 g (0.273M) of 5-ethyl-4,5-dihydro-4-hydroxy-9,10-dimethoxy-2-methyl-4-n-propyl-dibenz[cd,f]indole in 2000 ml ethanol is added with stirring to a suspension of 322 g (4.928M) of zinc dust and 74.3 g (0.273M) of mercury(II) chloride in 2000 ml distilled water. The reaction mixture is refluxed, 450 ml of 18% hydrochloric acid are added dropwise over a period of 15 minutes and the mixture is refluxed overnight with stirring. The mixture is then cooled to room temperature, filtered and the zinc amalgam is washed with 500 ml methylene chloride. The filtrate is made alkaline with 1 liter of concentrated NH4OH and extracted three times with methylene chloride (700 ml each time). The combined organic phases are washed with water, dried and evaporated. The resultant oil is chromatographed on silica gel using methylene chloride with 2% methanol to give the title compound as an oil.

Provenance & Evidence